#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/59/1505965.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1505965
loop_
_publ_author_name
'Yin, Guodong'
'Zhou, Baohan'
'Meng, Xianggao'
'Wu, Anxin'
'Pan, Yuanjiang'
_publ_section_title
;
 Efficient C-C double-bond formation reaction via a new synthetic
 strategy: a self-sorting tandem reaction.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2245
_journal_page_last               2248
_journal_paper_doi               10.1021/ol060541e
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C17 H12 Cl2 O2 S'
_chemical_formula_sum            'C17 H12 Cl2 O2 S'
_chemical_formula_weight         351.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.433(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0885(17)
_cell_length_b                   9.0949(10)
_cell_length_c                   11.4633(12)
_cell_measurement_reflns_used    3263
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.59
_cell_volume                     1624.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8962
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  0.9013
_exptl_absorpt_correction_T_min  0.8570
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0507P)²+0.1032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                2478
_reflns_number_total             3176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060541esi20060305_075936.cif
_cod_data_source_block           t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.42673(13) 1.1618(2) 0.4177(2) 0.0518(5) Uani 1 1 d .
C2 C 0.37383(14) 1.0943(2) 0.4775(2) 0.0574(5) Uani 1 1 d .
H2 H 0.3581 1.1417 0.5406 0.069 Uiso 1 1 calc R
C3 C 0.34386(13) 0.9544(2) 0.44291(18) 0.0508(5) Uani 1 1 d .
H3 H 0.3082 0.9073 0.4836 0.061 Uiso 1 1 calc R
C4 C 0.45232(13) 1.0931(2) 0.3258(2) 0.0586(6) Uani 1 1 d .
H4 H 0.4900 1.1393 0.2879 0.070 Uiso 1 1 calc R
C5 C 0.42131(13) 0.9548(2) 0.29078(18) 0.0526(5) Uani 1 1 d .
H5 H 0.4374 0.9081 0.2276 0.063 Uiso 1 1 calc R
C6 C 0.36635(11) 0.88382(19) 0.34864(16) 0.0412(4) Uani 1 1 d .
C7 C 0.33030(12) 0.7379(2) 0.30298(17) 0.0452(4) Uani 1 1 d .
C8 C 0.29259(12) 0.6453(2) 0.38098(18) 0.0466(5) Uani 1 1 d .
H8 H 0.3030 0.6676 0.4625 0.056 Uiso 1 1 calc R
C9 C 0.24320(12) 0.5288(2) 0.33712(17) 0.0461(4) Uani 1 1 d .
C10 C 0.22138(12) 0.4833(2) 0.20586(18) 0.0497(5) Uani 1 1 d .
C11 C 0.15457(12) 0.5663(2) 0.11748(18) 0.0457(5) Uani 1 1 d .
C12 C 0.13164(13) 0.5194(2) -0.00116(18) 0.0537(5) Uani 1 1 d .
H12 H 0.1584 0.4373 -0.0238 0.064 Uiso 1 1 calc R
C13 C 0.06977(14) 0.5925(2) -0.0861(2) 0.0578(5) Uani 1 1 d .
H13 H 0.0547 0.5606 -0.1657 0.069 Uiso 1 1 calc R
C14 C 0.03082(13) 0.7133(2) -0.05129(19) 0.0542(5) Uani 1 1 d .
C15 C 0.05065(14) 0.7610(2) 0.0656(2) 0.0607(6) Uani 1 1 d .
H15 H 0.0228 0.8420 0.0879 0.073 Uiso 1 1 calc R
C16 C 0.11274(13) 0.6867(2) 0.14993(19) 0.0545(5) Uani 1 1 d .
H16 H 0.1266 0.7180 0.2297 0.065 Uiso 1 1 calc R
C17 C 0.23919(16) 0.4652(3) 0.57092(19) 0.0719(7) Uani 1 1 d .
H17A H 0.3007 0.4623 0.5894 0.108 Uiso 1 1 calc R
H17B H 0.2192 0.4005 0.6242 0.108 Uiso 1 1 calc R
H17C H 0.2207 0.5637 0.5809 0.108 Uiso 1 1 calc R
Cl1 Cl 0.46366(4) 1.33817(6) 0.46104(6) 0.0804(2) Uani 1 1 d .
Cl2 Cl -0.04787(4) 0.80458(8) -0.15854(6) 0.0799(2) Uani 1 1 d .
O1 O 0.33060(10) 0.69869(16) 0.20046(13) 0.0618(4) Uani 1 1 d .
O2 O 0.25397(10) 0.37297(16) 0.17757(14) 0.0674(4) Uani 1 1 d .
S1 S 0.19650(4) 0.40794(6) 0.41923(5) 0.0642(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C4 121.63(18)
C2 C1 Cl1 118.87(16)
C4 C1 Cl1 119.50(16)
C1 C2 C3 119.12(19)
C1 C2 H2 120.4
C3 C2 H2 120.4
C6 C3 C2 120.73(18)
C6 C3 H3 119.6
C2 C3 H3 119.6
C1 C4 C5 118.93(18)
C1 C4 H4 120.5
C5 C4 H4 120.5
C4 C5 C6 120.85(18)
C4 C5 H5 119.6
C6 C5 H5 119.6
C3 C6 C5 118.69(17)
C3 C6 C7 122.27(16)
C5 C6 C7 118.96(17)
O1 C7 C8 121.16(17)
O1 C7 C6 120.01(17)
C8 C7 C6 118.80(16)
C9 C8 C7 121.38(18)
C9 C8 H8 119.3
C7 C8 H8 119.3
C8 C9 C10 123.75(17)
C8 C9 S1 126.27(16)
C10 C9 S1 109.98(13)
O2 C10 C11 121.67(19)
O2 C10 C9 118.85(19)
C11 C10 C9 119.20(16)
C16 C11 C12 118.6(2)
C16 C11 C10 122.41(18)
C12 C11 C10 118.93(17)
C13 C12 C11 120.93(19)
C13 C12 H12 119.5
C11 C12 H12 119.5
C14 C13 C12 118.88(19)
C14 C13 H13 120.6
C12 C13 H13 120.6
C15 C14 C13 121.8(2)
C15 C14 Cl2 119.43(17)
C13 C14 Cl2 118.77(17)
C14 C15 C16 118.8(2)
C14 C15 H15 120.6
C16 C15 H15 120.6
C15 C16 C11 120.97(19)
C15 C16 H16 119.5
C11 C16 H16 119.5
S1 C17 H17A 109.5
S1 C17 H17B 109.5
H17A C17 H17B 109.5
S1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C9 S1 C17 103.34(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.364(3)
C1 C4 1.373(3)
C1 Cl1 1.7397(19)
C2 C3 1.383(3)
C2 H2 0.9300
C3 C6 1.380(3)
C3 H3 0.9300
C4 C5 1.376(3)
C4 H4 0.9300
C5 C6 1.389(2)
C5 H5 0.9300
C6 C7 1.490(3)
C7 O1 1.229(2)
C7 C8 1.465(3)
C8 C9 1.345(3)
C8 H8 0.9300
C9 C10 1.515(3)
C9 S1 1.7351(19)
C10 O2 1.213(2)
C10 C11 1.486(3)
C11 C16 1.384(3)
C11 C12 1.385(3)
C12 C13 1.378(3)
C12 H12 0.9300
C13 C14 1.372(3)
C13 H13 0.9300
C14 C15 1.369(3)
C14 Cl2 1.740(2)
C15 C16 1.381(3)
C15 H15 0.9300
C16 H16 0.9300
C17 S1 1.781(2)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17B O2 0.96 2.59 3.296(3) 130.7 4_566
C2 H2 O2 0.93 2.57 3.358(3) 142.8 4_576
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 C1 C2 C3 -1.4(3)
Cl1 C1 C2 C3 179.62(17)
C1 C2 C3 C6 -0.5(3)
C2 C1 C4 C5 2.3(3)
Cl1 C1 C4 C5 -178.72(17)
C1 C4 C5 C6 -1.3(3)
C2 C3 C6 C5 1.4(3)
C2 C3 C6 C7 -175.39(19)
C4 C5 C6 C3 -0.5(3)
C4 C5 C6 C7 176.42(19)
C3 C6 C7 O1 158.35(19)
C5 C6 C7 O1 -18.5(3)
C3 C6 C7 C8 -19.9(3)
C5 C6 C7 C8 163.31(18)
O1 C7 C8 C9 -12.6(3)
C6 C7 C8 C9 165.55(18)
C7 C8 C9 C10 -0.6(3)
C7 C8 C9 S1 178.57(14)
C8 C9 C10 O2 108.4(2)
S1 C9 C10 O2 -70.9(2)
C8 C9 C10 C11 -77.5(2)
S1 C9 C10 C11 103.19(17)
O2 C10 C11 C16 175.68(19)
C9 C10 C11 C16 1.8(3)
O2 C10 C11 C12 -2.6(3)
C9 C10 C11 C12 -176.57(16)
C16 C11 C12 C13 1.3(3)
C10 C11 C12 C13 179.73(17)
C11 C12 C13 C14 -0.1(3)
C12 C13 C14 C15 -1.3(3)
C12 C13 C14 Cl2 -179.52(15)
C13 C14 C15 C16 1.2(3)
Cl2 C14 C15 C16 179.48(16)
C14 C15 C16 C11 0.1(3)
C12 C11 C16 C15 -1.4(3)
C10 C11 C16 C15 -179.71(19)
C8 C9 S1 C17 -5.9(2)
C10 C9 S1 C17 173.35(15)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199833 ChemSpider
